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STEPHEN COLBERT: TRIUMPHANT IN DEFEAT: PART ONE (OF TWO)

In Bureaucracy, Business, Entertainment, History, Politics, Social commentary on May 26, 2026 at 12:05 am

 …A truly great man is ever the same under all circumstances. And if his fortune varies, exalting him at one moment and oppressing him at another, he himself never varies, but always preserves a firm courage, which is so closely interwoven with his character that everyone can readily see that the fickleness of fortune has no power over him.                                                                                              Niccolo Machiavelli, The Discourses       

Watching the last episode of The Late Show With Stephen Colbert was like watching a slow-motion execution—where the victim turns his demise into a rousing revival meeting.  

That episode, shown on Thursday, May 21, capped a hugely successful run of 10 years and eight months (September 8, 2015 to May 21, 2026). Broadcast on CBS against ABC’s Jimmy Kimmel Live! and NBC’s The Tonight Show Starring Jimmy Fallon, Late Night ranked as the highest-rated American late-night talk show.

And it held that ranking for nine consecutive seasons, marking the longest such streak in franchise history.

Stephen Colbert | WikiLists | Fandom

Stephen Colbert

But for all the adoring fans Colbert attracted during those years, he acquired one enemy who never forgot or forgave the slightest insult. And from 2015 onward, Colbert showered him with humorous, deadly accurate insults calculated to get under his paper-thin skin and stay there.

That enemy was Donald J. Trump.

Colbert started throwing thousands of barbs at Trump immediately after the real estate mogul launched his first campaign for President on June 16, 2015. These focused on Trump’s appearance, intelligence, family, policy shifts, criminality, legal troubles and commercial ventures.

Among the barbs:

  • “It’s true, this [Iran] war reached all of its objectives. It’s been weeks since anyone mentioned the Epstein files.”
  • After Trump threatened to destroy Iran but then agreed to a brief pause, Colbert paraphrased John Lennon’s famous peace anthem, singing: “All we are saying, is peace for two weeks.” 
  • “For my  MAGA viewers. The Trump golden cell phone has FINALLY arrived after a nine month delay. And it SUCKS. The only Trump item more disappointing after a nine-month wait was Eric!” 
  • Colbert often joked about Trump’s short attention span, comparing his mind to “nature’s most cunning opponent, the goldfish.”
  • Following Trump’s 34 felony convictions on May 30, 2024, for falsifying business records, Colbert joked that Trump had “more felonies than Baskin-Robbins has flavors.”

Head-and-shoulders shot of Trump with a serious facial expression, his right eye partly closed. He is wearing a dark blue suit, a pale blue dress shirt, a red necktie, and an American flag lapel pin. Parts of the image are slightly out of focus. The background is black.

Donald Trump

Colbert had a biting wit that never flinched at speaking truth to—and about—power. But Trump had a weapon that Colbert couldn’t match: Command of the Federal Communications Commission (FCC). 

And in its chair, Brendan Carr, he had a crony willing to destroy any network that dared to offend his thin-skinned boss, Donald Trump. 

Knowing Trump’s animosity toward nonwhites, Carr has brutally attacked any network-related company promoting Diversity, Equity and Inclusion (DEI). He ordered investigations into Comcast and the Walt Disney Company and threatened to revoke ABC’s broadcast license over the practices. 

On September 10, 2025, Right-wing propagandist Charlie Kirk was shot at Utah Valley University in Orem, Utah.

In September 2025, Carr pressured Disney, which owns ABC, to suspend comedian Jimmy Kimmel over comments he had made about the assassination. On September 17, Disney caved and suspended Kimmel.

Brendan Carr

Kimmel had actually called the murder “senseless.” What enraged Right-wing Americans was Kimmel’s noting that “the MAGA gang is desperately trying to characterize this kid who murdered Charlie Kirk as anything other than one of them and doing everything they can to score political points from it.” 

This was actually true—and all the more embarrassing to Republicans because of it. The Trump administration and its MAGA cult have tried to portray Tyler Robinson, the man accused of shooting Kirk, as a radical liberal.

He is not.

Debbie Robinson, his grandmother, said most of the family are Republicans—and that Tyler’s father, Matt, is a staunch supporter of Donald Trump.  

Disney/ABC reinstated The Jimmy Kimmel Show on September 23  after a massive public backlash, a steep drop in Disney’s stock value, and a widespread Hollywood boycott.

Photo of Kimmel smiling at his late-show desk

Jimmy Kimmel

Paramount had recently paid Trump $16 million to settle a lawsuit he had brought against the CBS news show, 60 Minutes. He claimed that it had misleadingly edited a pre-election interview with then Vice President Kamala Harris to boost her election chances in 2024. CBS’ attorneys and a number of legal experts had said that the lawsuit was “completely without merit.”

On July 14, 2025, after returning from a multi-week break, Colbert said: “While I was on vacation, my parent corporation, Paramount, paid Donald Trump a $16 million settlement over his ‘60 Minutes’ lawsuit.

“As someone who has always been a proud employee of this network, I am offended. And I don’t know if anything will ever repair my trust in this company, but just taking a stab at it, I’d say $16 million would help.

“I believe this kind of complicated financial settlement with a sitting government official has a technical name in legal circles—it’s big fat bribe.

Colbert didn’t know it, but the axe was about to fall.